藥物詳細合成路線

Name	Cefteram pivoxil;Ro-19-5248;T-2588;Tomiron
Chemical Name	[6R-(6alpha,7beta)]-7-[2-(2-Amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester;(6R,7R)-7-[2-(2-Amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid pivaloyloxymethyl ester
CAS	82547-81-7
Related CAS	82556-89-6 (monoHCl)
Formula	C22H27N9O7S2
Structure
Formula Weight	593.64459
Stage	上市-1987
Company	Toyama (Originator), Showa Sangyo (Comarketer)
Activity/Mechanism	Antibiotics, ANTIINFECTIVE THERAPY, DENTAL AGENTS, Cephalosporins
Syn. Route	1

Route 1 the condensation of 7-aminocephalosporanic acid (i) with 5-methyltetrazole (ii) by means of bf3 ethyl ether in sulfolane gives 7-amino-3-(5-methyl-1,2,3,4-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid (iii), which is esterified with pivaloyloxymethyl iodide (iv) by means of triethylamine in dmf yielding the corresponding ester (v). finally, this compound it condensed with 2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (vi) by means of pocl3 and dimethylacetamide in ch2cl2. List of intermediates No. (3ar,6as)-4-[(z)-2-bromo-4-methyl-3-oxo-1-octenyl]hexahydro-2h-cyclopenta[b]furan-2-one (i) 2-hydroxy-6-methoxybenzaldehyde (ii) ethyl 5-bromopentanoate (iii) 5-[3-(benzyloxy)-2-formylphenoxy]pentanoic acid (iv) 2-iodobenzoic acid (v) 1-chloro-3-[4-(2-methoxyphenyl)-1-piperazinyl]-2-propanol (vi) Reference 1:     hirakawa, t.; imaizumi, h.; inaba, t.; konishi, y.; narita, h.; sadaki, h.; saikawa, i.; tai, m.; taki, h.; watanabe, y. (toyama chemical co., ltd.); cephalosporins. au 8549860; au 8549863; de 3137854; us 4489072 . Reference 2:     serradell, m.n.; castaner, j.; cefteram. drugs fut 1986, 11, 9, 732.

來源:藥化網

作者:藥化小編

摘要:本文合成路線介紹的是藥物中文名頭孢特侖新戊酯；英文名Cefteram pivoxil;Ro-19-5248;T-2588;Tomiron；CAS[82547-81-7]

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